The synthesis of nogarols, nogalamycin, 6-deoxy-6-demethyl-tetracycline analogs and olivin are the specific aims of this proposal. The nogarols and nogalamycin are potent anticancer agents. Olivin is part of olivomycin, which exhibits antibiotic and anticancer activity. The tetracycline analogs should exhibit better pharmacokinetic character than many tetracyclines. The basis for the nogarol and tetracycline syntheses is a tandem Claisen-Diels-Alder sequence which was developed in our laboratory. Additionally, a very direct route to the anthracycline skeleton is described. It should be ideal for the construction of many 11-deoxyanthracycline analogs.